


One Night Stand

by DeansCherryPie67



Series: Dean Winchester FanFics [1]
Category: Supernatural
Genre: F/M, One Night Stand With Dean Winchester, So If You Guys Want You Can Give Me Suggestions in The Coments:D, also if you guys recognize any of my stories from wattpad, also my usernames for wattpad is SupernaturalLover15, feel Like This Short Story Could Use Work, send me a quit comment and tell me how you feel
Language: English
Status: Completed
Published: 2015-09-27
Updated: 2015-09-27
Packaged: 2018-04-23 15:30:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,147
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4882099
Author URL: https://archiveofourown.org/users/DeansCherryPie67/pseuds/DeansCherryPie67
Summary: <blockquote class="userstuff">
              <p>"Man, I could get any woman to go home with me." Dean said around another bite of his burger, Sam sat back and chuckled, taking a swig if his beer.</p>
<p>"Sure you could." He said sarcastically.</p>
<p>"You doubting my skills?" Dean questioned after a minute and Sam shrugged.</p>
<p>"No, just dont think you could get any woman." Dean chuckled lowly, sipping his beer as he finished up his fries.</p>
<p>"You wanna make it a bet?" Dean asked and Sam chuckled, letting his eyes take on a mischievous glow as they always did when Dean said the word bet.</p>
<p>"Sure, I'll point out a woman and you have to get at least her number to win. If you lose. . .hmm. . .you have to do the laundry for a month. The same for me if I lose." Sam suggested and Dean nodded, sweeping his hand in a gesture that said "get to choosing, Sammy boy." Sam took a few minutes to look around the room, then smiled when his eyes landed on her again.</p>
<p>"Her." Sam said and Dean looked up, smirking softly.</p>
<p>"Watch and learn Sammy boy."</p>
            </blockquote>





	One Night Stand

**Author's Note:**

> None of the characters belong to me, nor does the show they're portrayed in. Thanks and happy reading!

Dean was currently sitting at a table, Sam in front of him as they talked over the day's work. They had been successful in the easy salt-and-burn, which gave them a little time until their next case. Time to unwind and relax, which meant women for Dean. Sam, knowing this, begins to look around the room at all the available women. But one stuck out for him, a young woman wearing glasses sat alone at a table. She was way too beautiful to be there alone but she didn't seem to be waiting on anyone, just casually looking around the room at all the people. Sam's smile turned wicked as he looked back at Dean as he shoved a handful of fries into his mouth.

"Who you gonna choose?" Sam set the bait and let Dean swallow before he looked around the room, shrugging his response.

"Don't know yet, although I see a few that I'm rather interested in." He said and Sam nodded, he glanced back at the woman still observing everyone.

"Bet you'll get turned down at least once." Sam offered casually, as he always would.

"Man, I could get any woman to go home with me." Dean said around another bite of his burger, Sam sat back and chuckled, taking a swig if his beer.

"Sure you could." He said sarcastically.

"You doubting my skills?" Dean questioned after a minute and Sam shrugged.

"No, just dont think you could get any woman." Dean chuckled lowly, sipping his beer as he finished up his fries.

"You wanna make it a bet?" Dean asked and Sam chuckled, letting his eyes take on a mischievous glow as they always did when Dean said the word bet.

"Sure, I'll point out a woman and you have to get at least her number to win. If you lose. . .hmm. . .you have to do the laundry for a month. The same for me if I lose." Sam suggested and Dean nodded, sweeping his hand in a gesture that said "get to choosing, Sammy boy." Sam took a few minutes to look around the room, then smiled when his eyes landed on her again.

"Her." Sam said and Dean looked up, smirking softly.

"Watch and learn Sammy boy." Dean mumble and Sam smirked as he watched Dean stand after wiping his mouth clean. He walked over in her direction and sat at the table next to hers, the one filled with women. Sam was about to jump up and tell him that he was talking with the wring girl when he remembered this trick, he chuckled and watched Dean speak with a few of the women before he glanced up at Sam, sending him a wink. One of the women was in the middle of talking when he looked over at the woman Sam had pointed out. Sam smirked a little and was confident that Dean wouldn't get her number, let alone a one night stand, from this woman. He leaned over and said something, her cheeks turned a gentle shade of pink before she smirked up at him. They talked for a while and she laughed softly, scooping up her purse before walking out. Dean watched her walk away, smirking as his eyes followed her put the door. He stood and walked back over to the table, placing his bottle down by his empty plate.

"She refused you, huh?" Sam asked and Dean shook his head, watching the door.

"She's waiting in the car." He said and Sam choked on his beer, eyes wide. He had been so certain that she'd refuse him, he sighed and placed his beer down.

"Shit, Could you at least drop me off at the library?" Sam asked and Dean chuckled, shrugging.

"I'll be in the car, hurry up." He said before he walked off, leaving Sam trying to figure out how he was so good at picking up women.

. . . . .

Dean slid into the driver side of the impala and cranked it up, smirking over at the woman, who's name was Jenna.

"If you don't mind, I have to drop off my little brother at the library before we head back to the motel." He said and she nodded.

"That's fine." She drawled in her southern accent, the back door opened and Sam slid in, having to duck his head, behind Dean and closed the door. Dean stopped in front of the library and Sam stepped out, closing the door behind him. Dean pulled away from the curb and glanced at Jenna, she was tapping her index finger to the beat of the song playing.

"You like Metallica?" He asked her and she looked up at him with a smirk, nodding. He chuckled and looked back to the road, turning the radio up a little. Soon, he was killing the engine in front of the room and she was stepping from the passenger side. He took the key from his pocket and opened the door for her, closing it back when he'd stepped through. He tossed the keys down onto the table and she placed her bag on the floor next to the door, taking her jacket off before she hung it on the back of a chair at the table. She chuckled and Dean looked up at her, scrunching his eyebrows.

"I've never done anything like this before." She confessed and he nodded, walking to her side as she took a deep breath. She looked up into his eyes as he lifted his hands to her face, lifting her glasses from her nose, placing them on the table next to his bed.

"We can go slow then." He whispered and she smiled softly, nodding as he leaned his face into hers. His lips touched hers finally and she was putty in his hands, his lips slid across hers for a long moment before he pulled away. He looked down into her eyes and she took a deep, nervous breath to calm herself.

"Would you like a beer?" He asked and she smiled, nodding. He turned his back and she licked her lips, touching them gently with her fingertips. She sat on the bed and he brought her a beer, popping the top on it before handing it to her. He sat next to her and took a sip of his own before he looked down at her again, Dean had never been one for gentle and slow but there's always a first time for everything. She placed her beer down and leaned her face into his, it took him a moment before he responded but when he did, his lips were soft and gentle. He pulled away and placed his own beer on the table before turning back to her, she placed her lips against his and his body responded before he could think. He pulled her onto his lap and layed back, hands finding her thys as he kissed her harder. He pulled away when he realized what he'd done and she looked surprised.

"Sorry." He mumbled and she smirked, nodding.

"That's okay, please." She started, "Take control." She whispered the last bit and he moaned softly, leaning his head back before he quickly pushed her over onto her back. She smirked and he kissed down her jaw, slipping his hands under her shirt. She shivered, moaning softly as he sucked at the nape of her neck.

"Oh Dean." She whispered and he moaned again, looking into her eyes.

"You make my name sound so good." He whispered and she chuckled softly, he stood and she watched as he slipped his shirt over his head. She leaned up and ran her fingers over his stomach, tracing his abs, up to his chest where she traced his pecks and circled his nipples.

"Mm, no one's ever paid this much attention to me before." He mumbled, mostly to himself, and she smirked sexily up at him. She stood in from of him, body so close he could feel the slight tremble as she slipped her own shirt off. He reached down and unbutton her jeans, sliding the zipper down before he slowly slid them down to the floor, following them. She smiled as he kissed back up her left thy, leaving little kisses all the way up her stomach, past her breasts before he ended at her lips again. She unbuckled his belt, pulling it through the loops before she worked the button and zipper down, having to really work at pulling the zipper past his hard-on. She rubbled his thys, making sure to get as close as she could to his dick without touching him. He grunted, pulling her body closer to his as he stepped from his jeans, leaning her back against the bed. He kissed down her neck, leaving a small hickey where her sweet spot was, forcing a moan from her lips. He started down her chest, ending just above the middle of her breasts before he sat up, bringing her with him. She allowed him to take her bra off, tossing it into the floor before he leaned her back down, starting his journey again. He paid extra attention to both her breasts, licking and sucking until she was writhing beneath him.

"Oh Dean, please. I-I'm ready." She moaned, lost in lust.

"I wanna make this good for you, so when you're with someone else you'll think of me. And how good tonight was. I want you to remember tonight, remember every little detail. I wanna make this so good, no one will ever live up to it." He said and she moaned loudly, begging him once again to hurry. He kissed down her stomach, slipping her panties down, tossing them into the floor as well. He kissed the inside of her thys, teasing her until she begged again, bucking her hips into him. He lapped softly at her clit, her hand found his hair and she cursed softly. He chuckled, letting his tongue put a little more pressure on her clit before he sucked gently at it. She arched her back into the air, a soft cry leaving her lips before he pulled away, licking a line from her entrance to her clit, ending with him sucking at it again.

"Yes, yes. Oh God, Dean." She mumbled and he let his breath wash over her skin, taking two of his fingers into his mouth before slipping them into her, teasing her g-spot.

"Ugh, Dean. Shit, yes. Oh, yes!" She said as his mouth found her clit again, pumping his fingers in and out of her quickly. Her hands were in his hair, forcing his face closer to her as she neared her orgasm.

"Oh shit, Dean. I'm gonna--oh--I'm gonna cum, Dean." She moaned and he nipped her clit slightly.

"Come on, darlin'. Cum for me, I wanna hear you scream my name." He whispered against her clit and she did, bucking her hips into the air, she cried out and he fucked her with his fingers through her orgasm, teasing her clit.

"Oh, Dean! Shit, yes! Yes! Mmm, so good. Oh God, Dean. That was so good." She whispered the last part and he sucked his fingers dry before he wiped his mouth on the sheet. He kissed up her body again, leaving a soft peck on her lips before he rolled onto his back.

"You ready, darlin'?" He asked and she nodded, he slipping his boxers off and grabbed a condom from the drower, slipping it on to his cock. He straddled her waist again, kissing her passionately before he looked down, about to push into her before she said his name.

"Dean." She purred and he looked up at her, hoping she wouldn't ask him to stop.

"Yeah?" He asked and she smiled softly, caressing his cheek.

"I want it to last, I dont wanna fuck and be done with it. I want tonight to last, I want you to take it slow." She whispered and he smirked, kissing her again before he pulled away to nod.

"Anything you want. I'll do anything for you." He said and she nodded for him to continue.

"I'm gonna make you feel so good." He whispered as he slipped into her, moaning at the feel. She wrapped her arms around his neck and moaned loudly, he filled her so well, like they were made for this. He took a moment for them to adjust before he began to thrust into her slowly. She kissed him gently as she bed squeaked softly, their bodies had begun to sweat already, their fluids mixing, creating friction between their skin. He quickened a long moment later, moans becoming animalistic almost.

"Nngh, you feel so good. God, you're so tight." He moaned softly, kissing her neck as she moaned his name.

"Oh Dean, I-I wanna--oh yes--I wanna ride you, Dean. Please." She begged and he moaned a sound that had her blood boiling. He turned onto his back and she straddled him, hands finding his chest for support. He held his cock steady as she pushed him into her. She started off slow again, reaching a nice speed after a moment, he grunted and she leaned down so her hands were resting on either side of his face. He wrapped his arms around her back and she let herself quicken again, at the rate she was going, she was going to cum sooner than she'd hoped but somehow she knew they'd have all night.

"Dean, I'm gonna cum." She whimpered after another few moments, he moaned and placed his hands against her hips, forcing her to quicken, creating a soft slap as their thys connected in the middle.

"Oh Jenna, cum baby. Cum for me. Oh fuck, yes. Jen, fuck. Come on baby." He half pleaded, half commanded. Her muscles contracted around him and she cried out, forcing her hips to quicken as much as she could. He threw his head back, fucking up into her as he cried her name. His voice grew deep and husky, grunts turning into loud little ah's the closer he got and soon after, he pushed himself over the edge. He bucked his hips into the air, her name leaving his lips as he came.

"Yes, fuck baby. Oh God, Jen! Ugh!" He cried as his fingers dug into her hips, she didn't mind the pain though, besides, he was too far gone to understand her even if she did ask him to stop. She stopped moving after a minute and layed on her side, a soft, content moan leaving her lips.

"I thought we were taking it slow?" He asked between breaths and she chuckled, he removed the condom before walking into the bathroom, returning a moment later, laying back beside her as they caught their breath. She leaned up and placed her lips against his, he kissed her back and they layed there like that, hands exploring one another's bodies as their tongues touched.

"I'm happy I could experience this with you." She whispered after a moment and he smiled despite the nervous feeling in his gut, he began to hope she wasn't going to get attached. He couldn't take care of her and Sammy at the same time, he had a hard enough time with just Sam. He placed his lips on hers again and kissed her with all his might, pushing her over again before slipping on another condom.

"This time, Dean. I want you to treat me like you would anyone else." She whispered and he looked into her eyes, just to make sure she was serious.

"Are you sure?" He asked and she nodded, bringing his lips down to hers before she pulled away.

"Just remember, you asked for it." He said and she chuckled. He tapped her thy to signal for her to turn over and she did, laying on her stomach as he settled over her.

"Spread your legs wide." He said and she did as he said again, moaning loudly as he pushed into her slowly. Once he was buried in her, he began the brutal thrusts, fucking her good and proper.

"Oh-h Dean! Y-yes, fuucckk!" She cried and he moaned, placing his arms so he was leaned over her back, hands propped on either side of her head. The headboard had begun to hit up against the wall as Dean began to grunt, it didn't take but a few moments for her to cum. She reached her right hand down to grasp at his thy as her muscles constricted around his length, sending him into his own orgasm. He gripped tightly onto the pillows on either side of her head, snapping his hips into her, creating soft slaps as their skin met. He went still a few moments later and she moaned as he pulled out of her, she let out a deep breath as he got up to discard of the condom again. She rolled onto her back, catching her breath as he carried the trash can into the room, placing it next to his bed before he layed down on his back, she let out a soft chuckle and looked up at the ceiling. Once they'd caught their breath, they were at it again, they just couldn't seem to get enough of each other. They had been in the middle of their orgasms when Sam walked in, Jenna was too out of it, consumed in lust but Dean looked up. His mouth was open, pants leaving his lips as his hips slowed their pace. Sam didn't seem to be able to move, his feet were glued to the floor as Dean pulled the cover up, hiding the both of them behind it. After Jen had recovered and she had realized what was happening, Dean chuckled loudly.

"You just gonna stand there, Sammy?" Dean asked and Sam seemed to snap out of it because he slammed the door and Dean hears the impala's door open before it closed again, he'd be sleeping there for the night. A little while later, she was sitting up in the bed and stretching her arms above her head.

"I guess I should go." She said and he looked down at the sheets between them.

"I dont do this too often but. . .you can stay if you'd like." He said, tone almost shy and this surprised her.

"I didn't take you for the type, Dean." He chuckled softly, nodding.

"Well, I'm not really but. . ." His sentence was cut off when she placed her lips against his, pulling the sheet over her body again before she pulled away and layed on her side of the bed.

"Good night, Jen." He whispered into her ear and she smirked, kissing him once more before she turned onto her left side.

"Good night, Dean." She responded and they both drifted off to sleep.


End file.
